Too Scared To Ask For The Sale? Keep This In Mind.

Jake LorraineBlog, Popular Articles 8 Comments

One of the greatest salespeople I’ve ever known was “Tony D”, from Troy NY, and I was extremely lucky to have him as an employee. Sadly he passed away in 2014 but I learned an awful lot from him even though our style of selling was very different.

(don’t mind the terrible pic. If he saw someone taking his picture he’d probably grab the camera and shove it up their butt.)

Tony was everything you can imagine of the typical “direct salesman” — heavy addiction to gambling included. He’d cash a $3k commission check on Friday and be sleeping in his car in our parking lot on Tuesday to avoid his landlord.

I could outsell Tony in terms of closing percentage and sales price, but he was absolutely untouchable as far as profit. Where I’d end up discounting 20-30% he’d rarely ever get less than full profit.

I wish I spent more time with him talking sales but since he didn’t exactly need training or guidance we never really found ourselves chatting about it.

There’s one thing that stuck with me forever, though.

Tony’s car was in the shop one day so I sent another rep, Matt, to drive him around. It must have killed him to split commissions but it was better than not making any money. They come back with a sizeable deal and Matt tells me:

“I couldn’t believe it, Jake, Tony just basically rattled off benefits, looked at the guy and said “it’s $2,000, you gonna make a move?  … And he bought!”.

This didn’t particularly surprise me, after all it was Tony D,  the guy I once witnessed tell one of our clients on the phone that if he couldn’t come up with another thousand he “didn’t deserve to be in business” (and the guy DID come up with another thousand!).

I also was told by one of his clients that he had told her “I’m gonna go outside and have a cigarette, you call who you need to to get the money for this”. 

[I should note that the way Tony said these things were in a tone that was always very concerning, not condescending. It was all in his tone that prevented him from coming off as confrontational].

Since Tony was there in the room with us, I figured we’d have a laugh about it all.

But he didn’t laugh.

He didn’t think it was funny.

Instead, he said something surprisingly profound:

“Why not say what you want? The worst they can say is no.”


Sure I had heard that phrase before but it made nowhere near the impact as it did that very moment.

So many times we have a great product, great pitch, great pricing … but we get so nervous and frightened to ask for the sale that we end up discounting out of fear. We have visions of being laughed at, condemned, humiliated, shunned, crucified, or whatever ridiculous mirage our brains seem to concoct.

But if you’ve got a good product and price … and they could benefit from it …. why not ask?

Or better yet, in Tony D. fashion …simply direct them.

The upside is huge, especially when you’re asking for something with big profits and high value. Be proud of it, the rewards for standing up and not discounting out of fear are worth it. The best thing is you make a hell of a lot more money.

The worst?

They say no.

Big friggin deal.



Comments 8

  1. Wow, sounds like my kinda guy… apart from the frivolity with his money. You don’t run across people like him often, and somehow they don’t stick around long.

    “The only thing we have to fear is fear itself.”

    1. Post
  2. The beauty with selling advertising space is you can come up with long term packages, say for the first time clients, “normally it’s 12 months but I can’t ask you for that because this is your first time with us, so I recommend 6 months to try.”

    You aren’t discounting price, you are discounting time!

    Going in with a price with an outrageous number to start with, say ..”I can’t ask you 100k but I’ll let you have it for $698 if you can make a decision now.”

    You say it in a light hearted way.

    It’s pre-framing with a large number to get acceptance of the number you want., therefore the real number you want doesn’t seem so high and it’s very rare the buyer tries to lower the price from there on in.

    In both cases, it’s as if you already have conceded on some point which means it’s against social
    norms to get further concessions when the other person has already conceded to start with.

    Then you can nibble more time on the agreement as if it’s an afterthought say another 3 months as it doesn’t sound much. This can be after they say no to that length to start with.

    We talk about this kind of stuff with my friend in London who sells ad space. After 5 months there he broke the monthly sales record.

    He’s won trips to South Africa, Australia and New Zealand, all paid for.

    1. Post

Leave a Reply

Your email address will not be published. Required fields are marked *